Phenethyl bromide → HCID 89862978, compound

HRID 1053682Notes

Reaction equation

HRID 1053682 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]([C@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(#N)C.CN(C=O)C>[CH2:29]([N:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]([C@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH:3]=[N:2]1)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 89862967HCID 89862967, compound

Product 1

HCID 89862978HCID 89862978, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a vial was added Intermediate 11B (110 mg, 0.383 mmol) in acetonitrile (0.7 mL) and DMF (0.7 mL) and potassium carbonate (159.0 mg, 1.148 mmol). The reaction was stirred for 10 min before (2-bromoethyl)benzene (106 mg, 0.574 mmol) was added. The resulting mixture was heated at 50° C. for 16 h. The reaction was quenched with water and extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated. The crude was purified by flash chromatography to give Intermediate 11C (116 mg, 0.296 mmol, 77.0% yield) as a white solid. LCMS=2.20 min [M+1]=392.3 (Method B).

Workup

  1. additionwas added
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-b51552c452614acea6762c15eda9f815
Source dataset
uspto-grants-2016_07
Patent number
US09394260B2

Reaction notes

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